Hydrocarbon Functionalization by the (Iodosylbenzene)manganese(IV) Porphyrin Complexes from the (Tetraphenylporphinato)manganese(HI)-Iodosylbenzene Catalytic Hydrocarbon Oxidation System. Mechanism and Reaction Chemistry

Journal of the American Chemical Society

Volumn 105, Issue 11, 1983, Pages 3515-3521

  Smegal, John A ^a   Hill, Craig L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845550273     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00349a025     Document Type: Article

References (26)

1. Hill, C. L.; Smegal, J.A. Nouv. J. Chim. 1982, 6, 287-289. (b) Hill, C. L.; Schardt, B. C. J. Am. Chem. Soc. 1980, 102, 6374-6375. (c) Groves, J. T.; Kruper, W. J., Jr.; Haushalter, R. C. J. Am. Chem. Soc. 1980, 102, 6375-6377. (d) Chang, C. K.; Ebina, F. J. Chem. Soc, Chem. Commun. 1981, 778-779. (e) Tabushi, I.; Koga, N. Tetrahedron Lett. 1979, 3681-3684. (f) Tabushi, I.; Koga, N. Tetrahedron Lett. 1978, 5017-5020. (g) Tabushi, I,; Yazaki, A. J. Am. Chem. Soc. 1981, 103, 7371-7373. (h) Tabushi, I.; Koga, N. J. Am. Chem. Soc. 1979, 101, 6456-6458. (i) Mansuy, D.; Bartoli, J.-F.; Chottard, J.-C.; Lange, M. Angew. Chem., Int. Ed. Engl. 1980, 19, 909-910. (j) Peree-Fauvet, M.; Gaudemer, A. J. Chem. Soc., Chem. Commun. 1981, 874-875.
2. For reviews on alkane activation by metal complexes see: (a) Shilov, A. E.; Shteinman, A. A. Coord. Chem. Rev. 1977, 24, 97-143. (b) Parshall, G. W. Acc. Chem. Res. 1975, 8, 113-117. (c) Webster, D. E. Adv. Organomet. Chem. 1977, 15, 147-188. (d) Sheldon, R. A.; Kochi, J. K. “Metal Catalyzed Oxidations of Organic Compounds” Academic Press: New York, 1981; pp. 206-211. (e) Shilov, A. E. Pure Appl. Chem. 1978, 50, 725-733. Also see: (f) Bergman, R. G.; Janowicz, A. H. J. Am. Chem. Soc. 1982, 104, 352-354. (g) Crabtree, A. H.; Mellea, H. F.; Mihelcic, J. M.; Quirk, J. M. J. Am. Chem. Soc. 1982, 104, 107-113 and references cited in each.
3. Recent reviews of cytochrome P-450: (a) Coon, M. J.; White, R. E. “Metal Ion Activation of Dioxygen” Spiro, T. G., Ed.; Wiley: New York, 1980; Chapter 2. (b) Gunsalus, J. C.; Sligar, S. G. Adv. Enzymol. Rel. Areas Mol. Biol. 1978, 47, 1-44. (c) Groves, J. T. Adv. Inorg. Biochem. 1979, 1, Chapter 4. (d) Chang, C. K.; Dolphin, D. Bioorg. Chem. 1978, 4, 37.
4. Schardt, B. C.; Hollander, F. J.; Hill, C.L. J. Am. Chem. Soc. 1982, 104, 3964-3972. (b) Smegal, J. A.; Schardt, B. C.; Hill, C. L. J. Am. Chem. Soc, preceding paper in this issue.
5. Abbreviation: TPP = mexo-tetraphenylporphinato dianion ligand.
6. The frequency of the Soret band for manganese(III) porphyrins is dependent on the axial ligand with the energy order being In strongly coordinating solvents where the axial ligands are displaced by solvent molecules, the frequency of the Soret band is independent of axial ligand. See: Boucher, L. J. Ann. N. Y. Acad. Sci. 1973, 206, 409-419.
7. For an example of a monomeric Mn(IV) EPR see: Richens, D. T.; Sawyer, D.T. J. Am. Chem. Soc. 1979, 101, 3681-3683.
8. An example of the EPR spectrum of a well-characterized manganese(III, IV) dimer is given in: Cooper, S. R.; Disrnukes, G. C.; Klein, M. P.; Calvin, M. J. Am. Chem. Soc. 1978, 100, 7248-7252.
9. Camenzind, M. J.; Hollander, F. J.; Hill, C.L. Inorg. Chem. 1982, 21, 4301-4308.
10. Camenzind, M. J.; Hill, C. L., unpublished work.
11. Similar properties of several chromium(III) tris(chelates) have been interpreted in this manner: Singer, L. S. J. Chem. Phys. 1955, 23, 379-388.
12. Boucher, L, J. Coord. Chem. Rev. 1972, 7, 289-329.
13. Maillard, B.; Ingold, K.U. J. Am. Chem. Soc. 1976, 98, 1224-1226.
14. Groves, J. T.; Kruper, W. J., Jr. J. Am. Chem. Soc. 1979, 101, 7613-7615.
15. Murmann, R. K. J. Am. Chem. Soc. 1974, 96, 7836-7837. (b) Sharpless, K. B.; Townsend, J. M.; Williams, D. R. J. Am. Chem. Soc. 1972, 94, 295-296.
16. Coon, M. J.; Vermilion, J. L.; Vatsis, K. P.; French, J. S.; Dean, W. L.; Haugen, D. A. ACS Symp. Ser. 1977, No. 44, 46. (b) Pryor, W. A. “Free Radicals in Biology” Pryor, W. A., Ed.; Academic Press; New York, 1976; p1. (c) Groves, J. T.; McClusky, G. A.; White, R. E.; Coon, M. J. Biochem. Biophys. Res. Commun. 1978, 81, 154-160.
17. Groves, J. T.; Kruper, W.J.; Nemo, T. E.; Myers, R.S. J. Mol. Catal. 1980, 7, 169-177, (b) Groves, J. T.; Nemo. T. E.; Myers, R. S. J. Am. Chem. Soc. 1979, 101, 1032-1033. (c) Chang, C. K.; Kuo, M.-S. J. Am. Chem. Soc. 1979, 101, 3413-3415.
18. Amey, R. L.; Martin, J.C. J. Am. Chem. Soc. 1979, 101, 3060-3065.
19. For other examples of iodinanyl radical oxidations see: (a) Banks, D. F.; Huyser, E. S.; Kleinburg, J. J. Org. Chem. 1964, 29, 3692-3693. (b) Tanner, D. D.; Van Bostelen, P. B. J. Org. Chem. 1967, 22, 1517-1521. (c) Tanner, D. D.; Gidley. G. C. J. Org. Chem. 1968, 33, 38-43. (d) Tanner, D. D.; Gidley, G. C. J. Am. Chem. Soc. 1968, 90, 808-809. (e) Heusler, K.; Kalvoda. J. Angew. Chem., Int. Ed. Engl 1964, 3. 525-538. (f) Tanner, D. D.; Gidley, G. C. Can. J. Chem. 1968, 46, 3537-3544.
20. Derivatives of iodosylbenzene were synthesized in an analogous mannrr to that given for iodosylbenzene but using the substituted iodobenzene precursor: cf. Lucas, H. J.; Kennedy, E. R.; Formo, M. W. “Organic Syntheses” Wiley: New York, 1955; Coll. Vol. 3, pp. 483-485.
21. Seven coordination in metalloporphyrin complexes of first-row transition metals has not been unambiguously established. A pseudo seven-coordinate iron porphyrin has been proposed for the oxygenated form of the capped iron porphyrin of Linard et al. in the presence of 1-Melm: Linard, J. E.; Ellis, P. E., Jr.; Budge, J. R.; Jones, R. D.; Basolo, F. J. Am. Chem. Soc. 1980, 102, 1896-1904.
22. Kochi, J. K. In “Free Radicals” Wiley: New York, 1973; Vol. 1 p. 594.
23. Purcell, K. F.; Kotz, J. C. “An Introduction to Inorganic Chemistry” Saunders: New York, 1980; p. 425. (b) Pearson, R. G.; Eligen, P. C. “Physical Chemistry, An Advanced Treatise” Eyring, H., Ed.; Academic Press: New York, 1975; Vol. VII Chapter 5.
24. Fleischer, E. B.; Krishnamurthy, M. J. Am. Chem. Soc. 1971, 93, 3784-3786.
25. Gouterman, M.; Hanson, L. K.; Khalil, G. E.; Leonstra, W.R. J. Chem. Phys. 1975, 62, 2343-2353.
26. Kirner, J. F.; Scheldt, W.R. Inorg. Chem. 1975, 14, 2081-2086. (b) Day, V. W.; Stults, B. R.; Tasset, E. L.; Day, R. O.; Marianelli, R. S. J. Am. Chem. Soc. 1974, 96, 2650-2652.